A short, stereoselective synthesis of (3R,4R)-4-acetoxy-3-[(R)-1'((t-butyldimethylsilyl)oxy)ethyl]-2-azetidin one, key intermediate for the preparation of carbapenem antibiotics.
A short stereoselective synthesis of the acetoxy azetidinone (1), an important precursor of several biologically active beta-lactam antibiotics, has been accomplished in seven steps and 32.8% overall yield from the easily available and inexpensive (R) ethyl 3-hydroxybutanoate.
Cozzi
F
F
Dipartimento di Chimica Organica e Industriale, Università di Milano, Italy.
Annunziata
R
R
Cinquini
M
M
Poletti
L
L
Perboni
A
A
Tamburini
B
B
D015780:Carbapenems / Q000138:chemical synthesis*; D007769:Lactams / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D013055:Spectrophotometry, Infrared; D013237:Stereoisomerism
C110742:4-acetoxy-3-(1'-((tert-butyldimethylsilyl)oxy)ethyl)-2-azetidinone; D015780:Carbapenems; D007769:Lactams